#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:48:56 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/91/7239168.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239168
loop_
_publ_author_name
'Pato-Doldán, B.'
'Gómez-Aguirre, L. C.'
'Bermúdez-García, J. M.'
'Sánchez-Andújar, M.'
'Fondado, A.'
'Mira, J.'
'Castro-García, S.'
'Señarís-Rodríguez, M. A.'
_publ_section_title
;
 Coexistence of magnetic and electrical order in the new perovskite-like
 (C3N2H5)[Mn(HCOO)3] formate
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              22404
_journal_paper_doi               10.1039/c3ra43165g
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C12 H16 Mn2 N4 O12'
_chemical_formula_weight         518.17
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.1962(3)
_cell_length_b                   12.3675(3)
_cell_length_c                   12.8155(3)
_cell_measurement_reflns_used    5164
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.885
_cell_measurement_theta_min      6.360
_cell_volume                     1932.44(8)
_computing_cell_refinement
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_data_reduction
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_refinement
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_solution
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'APEXII area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20812
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_T_max  0.7699
_exptl_absorpt_correction_T_min  0.5893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS Version 2008/1 (Sheldrick, Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+1.4855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0936
_reflns_number_gt                3904
_reflns_number_total             4863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra43165g.txt
_cod_data_source_block           1038874_b4_0s
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7239168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
C7 C 0.24590(19) 0.28245(16) 0.26199(15) 0.0132(4) Uani 1 1 d
C10 C 0.72439(18) -0.00233(15) 0.01267(15) 0.0118(4) Uani 1 1 d
C8 C 0.23006(18) 0.27129(16) -0.24181(15) 0.0128(4) Uani 1 1 d
C11 C 0.78496(18) 0.49548(15) -0.02580(16) 0.0137(4) Uani 1 1 d
C12 C 0.98699(19) 0.23116(17) 0.04883(16) 0.0145(4) Uani 1 1 d
C9 C 0.48335(18) 0.28929(16) 0.00525(15) 0.0132(4) Uani 1 1 d
H4 H 0.489(2) 0.2370(18) 0.0627(19) 0.012(6) Uiso 1 1 d
H1 H 0.989(2) 0.310(2) 0.071(2) 0.023(7) Uiso 1 1 d
H5 H 0.189(2) 0.339(2) 0.262(2) 0.029(7) Uiso 1 1 d
H6 H 0.288(2) 0.330(2) -0.237(2) 0.023(7) Uiso 1 1 d
H3 H 0.731(3) 0.492(2) -0.090(2) 0.040(9) Uiso 1 1 d
H2 H 0.788(3) 0.001(2) 0.062(3) 0.046(9) Uiso 1 1 d
H15 H 0.640(2) -0.0889(19) 0.2826(18) 0.013(6) Uiso 1 1 d
H13 H 0.427(2) 0.149(2) 0.3050(19) 0.020(6) Uiso 1 1 d
H16 H 0.513(2) -0.0819(19) 0.1160(19) 0.017(6) Uiso 1 1 d
10 H 0.062(2) -0.063(2) 0.093(2) 0.022(7) Uiso 1 1 d
H14 H 0.579(2) 0.054(2) 0.384(2) 0.027(7) Uiso 1 1 d
H11 H 0.151(2) 0.081(2) 0.2104(19) 0.020(6) Uiso 1 1 d
H17 H 0.398(2) 0.063(2) 0.137(2) 0.028(7) Uiso 1 1 d
H7 H -0.090(2) -0.125(2) 0.196(2) 0.030(8) Uiso 1 1 d
H9 H 0.039(2) 0.088(2) 0.359(2) 0.025(7) Uiso 1 1 d
H8 H -0.105(2) -0.037(2) 0.352(2) 0.034(8) Uiso 1 1 d
Mn1 Mn 0.23534(3) 0.25497(2) 0.01177(2) 0.00779(9) Uani 1 1 d
Mn2 Mn 0.73602(3) 0.24709(2) 0.01000(2) 0.00760(9) Uani 1 1 d
O7 O 0.19909(13) 0.23455(11) -0.15586(11) 0.0151(3) Uani 1 1 d
O1 O 0.57443(12) 0.31667(11) -0.03031(11) 0.0134(3) Uani 1 1 d
O4 O 0.89582(12) 0.18502(11) 0.04892(11) 0.0146(3) Uani 1 1 d
O9 O 0.07455(12) 0.18937(11) 0.02342(11) 0.0152(3) Uani 1 1 d
O6 O 0.77457(14) 0.25883(12) -0.15288(11) 0.0181(3) Uani 1 1 d
O10 O 0.16488(12) 0.41685(10) 0.00725(11) 0.0134(3) Uani 1 1 d
O12 O 0.39312(12) 0.32397(11) -0.02612(11) 0.0148(3) Uani 1 1 d
O5 O 0.67647(13) 0.08408(11) -0.00927(11) 0.0145(3) Uani 1 1 d
O2 O 0.69194(14) 0.25902(12) 0.17234(11) 0.0180(3) Uani 1 1 d
O8 O 0.30687(12) 0.09358(11) 0.02114(11) 0.0134(3) Uani 1 1 d
O11 O 0.28081(14) 0.25435(11) 0.17541(11) 0.0177(3) Uani 1 1 d
O3 O 0.79731(14) 0.41199(11) 0.02574(11) 0.0180(3) Uani 1 1 d
C6 C 0.09183(19) 0.03672(17) 0.21873(16) 0.0156(4) Uani 1 1 d
N4 N -0.04255(16) -0.08014(14) 0.21105(13) 0.0145(4) Uani 1 1 d
C4 C 0.04468(19) -0.03999(17) 0.15755(16) 0.0158(4) Uani 1 1 d
N5 N 0.03154(16) 0.04281(14) 0.30784(13) 0.0151(4) Uani 1 1 d
C5 C -0.04910(19) -0.02852(17) 0.30144(16) 0.0165(4) Uani 1 1 d
N2 N 0.44745(16) 0.04664(14) 0.18644(13) 0.0156(4) Uani 1 1 d
N1 N 0.54935(16) 0.04020(14) 0.32534(14) 0.0152(4) Uani 1 1 d
C2 C 0.5821(2) -0.04245(17) 0.26157(16) 0.0177(4) Uani 1 1 d
C1 C 0.46793(19) 0.09298(17) 0.27819(16) 0.0164(4) Uani 1 1 d
C3 C 0.5183(2) -0.03821(17) 0.17452(16) 0.0184(4) Uani 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O6 C7 O11 124.7(2) 4_566 .
O5 C10 O8 123.5(2) . 3_655
O2 C8 O7 123.6(2) 4_565 .
O3 C11 O10 124.4(2) . 3_665
O9 C12 O4 125.7(2) 1_655 .
O12 C9 O1 125.08(18) . .
O9 Mn1 O11 98.36(6) . .
O9 Mn1 O12 171.00(5) . .
O11 Mn1 O12 90.63(6) . .
O9 Mn1 O10 89.35(6) . .
O11 Mn1 O10 96.94(5) . .
O12 Mn1 O10 89.09(5) . .
O9 Mn1 O8 90.87(6) . .
O11 Mn1 O8 81.39(5) . .
O12 Mn1 O8 90.95(5) . .
O10 Mn1 O8 178.33(5) . .
O9 Mn1 O7 82.05(6) . .
O11 Mn1 O7 172.48(5) . .
O12 Mn1 O7 89.10(6) . .
O10 Mn1 O7 90.57(5) . .
O8 Mn1 O7 91.10(5) . .
O4 Mn2 O5 89.63(6) . .
O4 Mn2 O6 91.75(6) . .
O5 Mn2 O6 91.90(5) . .
O4 Mn2 O2 92.69(6) . .
O5 Mn2 O2 94.75(6) . .
O6 Mn2 O2 172.03(6) . .
O4 Mn2 O3 90.33(6) . .
O5 Mn2 O3 178.68(6) . .
O6 Mn2 O3 86.79(6) . .
O2 Mn2 O3 86.57(6) . .
O4 Mn2 O1 177.95(5) . .
O5 Mn2 O1 92.39(6) . .
O6 Mn2 O1 87.82(6) . .
O2 Mn2 O1 87.51(6) . .
O3 Mn2 O1 87.64(6) . .
C8 O7 Mn1 139.20(14) . .
C9 O1 Mn2 127.14(13) . .
C12 O4 Mn2 129.83(14) . .
C12 O9 Mn1 131.39(14) 1_455 .
C7 O6 Mn2 139.16(14) 4_665 .
C11 O10 Mn1 126.46(14) 3_665 .
C9 O12 Mn1 125.20(13) . .
C10 O5 Mn2 128.41(14) . .
C8 O2 Mn2 137.21(15) 4_666 .
C10 O8 Mn1 132.95(14) 3_655 .
C7 O11 Mn1 141.15(15) . .
C11 O3 Mn2 134.18(14) . .
C4 C6 N5 106.97(19) . .
C5 N4 C4 109.04(18) . .
C6 C4 N4 106.76(18) . .
C5 N5 C6 108.91(17) . .
N5 C5 N4 108.32(19) . .
C1 N2 C3 108.93(19) . .
C1 N1 C2 108.76(18) . .
C3 C2 N1 107.1(2) . .
N1 C1 N2 108.34(19) . .
C2 C3 N2 106.91(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 O6 1.247(2) 4_566
C7 O11 1.248(2) .
C10 O5 1.247(2) .
C10 O8 1.264(2) 3_655
C8 O2 1.242(2) 4_565
C8 O7 1.258(2) .
C11 O3 1.233(2) .
C11 O10 1.265(2) 3_665
C12 O9 1.237(3) 1_655
C12 O4 1.250(3) .
C9 O12 1.239(3) .
C9 O1 1.258(3) .
Mn1 O9 2.1309(15) .
Mn1 O11 2.1559(15) .
Mn1 O12 2.1710(15) .
Mn1 O10 2.1789(14) .
Mn1 O8 2.1804(13) .
Mn1 O7 2.1970(14) .
Mn2 O4 2.1420(15) .
Mn2 O5 2.1549(14) .
Mn2 O6 2.1560(14) .
Mn2 O2 2.1668(14) .
Mn2 O3 2.1798(14) .
Mn2 O1 2.2001(15) .
O9 C12 1.237(3) 1_455
O6 C7 1.247(2) 4_665
O10 C11 1.265(2) 3_665
O2 C8 1.242(2) 4_666
O8 C10 1.264(2) 3_655
C6 C4 1.350(3) .
C6 N5 1.376(3) .
N4 C5 1.327(3) .
N4 C4 1.373(3) .
N5 C5 1.322(3) .
N2 C1 1.326(3) .
N2 C3 1.370(3) .
N1 C1 1.322(3) .
N1 C2 1.374(3) .
C2 C3 1.345(3) .
